I'm running Quicken Classic Business & Personal R58.9 build 27.1.58.9 on Windows 11 Pro version 23H2 build 22631.4169. When I add an attachment it often doesn't show. If I close the program and reopen it, it might show but other attachments may then disappear. It seems to be totally random. I have validated my Quicken file with no change in this behaviour. It always used to work but stopped after a recent update to the software.